Tutorial on How to Name Carbohydrates

Carbohydrates:
Carbohydrates are known as sugar and composed of monosaccharides, disaccharides, and
polysaccharides. Monosaccharides cannot be broken down into simple sugar whereas
disaccharides and polysaccharides can be broken into simple sugars. Saccharides mainly consist
of carbon, hydrogen, and oxygen. A monosaccharides general formula is CnH2nOn, where the
integer n is at least 3 and rarely more than 6. Monosaccharides also contain the hydroxyl
(alcohol, OH) functional group, whereas disaccharides and polysaccharides contain both the
hydroxyl (alcohol, OH) functional group and a glycosidic bond between two simple sugar
molecules.
How to Name Acyclic Monosaccharide:
Acyclic monosaccharides have three different characteristics: the number of carbon atoms it
contains, its D or L configuration, and the placement of its carbonyl group (aldehyde or ketone).
These characteristics are combined to name monosaccharide carbohydrates.
Three carbon monosaccharides are called trioses, four carbon are called tetroses, five carbon are
called pentoses, six carbon are hexoses, and so on. The number of carbon atoms in a molecule is
used in the suffix of carbohydrate naming.

This sugar is pentose because

it has 5 carbons.

This sugar is hexose

because it has 6 carbons.

The carbonyl group is placed at the beginning of the saccharide. If the carbonyl group is an
aldehyde (more common in carbohydrates), then the monosaccharide is an aldose, and if the
carbonyl group is a ketone, then the monosaccharide is a ketose.

This sugar has an aldehyde functional

group so it is an aldose.

This sugar has a ketone functional

group so it is a ketose.

A monosaccharide is given D configuration if the hydroxyl group is to the right of the last
stereocenter in a Fischer projection, whereas L configuration is given if the OH is to the left of
the last stereocenter carbon. D or L is usually put in the beginning of the carbohydrate when
naming the molecule.
Note: Designation of D or L relates the configuration of a given molecule and does not specify the sign (+ or -) of
rotation of plane-polarized light.

This sugar has L configuration because

OH is to the left of the last stereocenter.

This sugar has D configuration because

OH is to the right of the last stereocenter.

Putting all the concepts together:

L-aldopentose

More examples:

This is D-aldopentose because the OH (circled) is

located to the right of the last stereocenter carbon.
It is an aldopentose because there are 5 carbons,
which gives it the suffix pentose and it contains
an aldehyde, which gives it the prefix aldo.

D-ketohexose

This is D-aldohexose because OH (circled) is

located to the right of the last stereocenter carbon.
It is an aldohexose because
there are 6 carbons, which gives it the suffix
hexose and it contains an aldehyde, which gives
it the prefix aldo.

This sugar is L-aldohexose because OH (circled) is

located to the left of the last stereocenter carbon.
It is an aldohexose because
there are 6 carbons, which gives it the suffix
hexose and it contains an aldehyde, which gives
it the prefix aldo.

How to name Cyclic Monosaccharide

Cyclic monosaccharides mostly consist of 5 or 6 carbon ring. 5 carbon rings have the suffix
fruscose and 6 carbon rings have the suffix pyranose. Also, when acyclic molecules are turned
into cyclic molecule, it creates a chiral center at the anomeric carbon and this gives rise to and
anomers. means that the anomeric OH and CH2OH groups are trans whereas means
anomeric OH and CH2OH groups are cis. These anomers are placed in the beginning in naming
cyclic carbohydrates.
This concept is shown in the examples below:

This is because OH and CH2OH are cis.

This is because OH and CH2OH are trans.

This sugar is -galactopyranose

because there are 6 carbons, which gives it the suffix
pyranose and since the molecule is galactose,
it has the prefix galacto.

This sugar is -glucopyranose because

there are 6 carbons, which gives it the suffix
pyranose and since the molecule is glucose,
it has the prefix gluco.

How to Name Cyclic Disaccharides

A disaccharide is two monosaccharide units linked by a glycosidic bond. The linkage between
these two bonds is labeled by the carbon that they are attached to. For example, in both maltose
(Figure 1) and cellobiose (Figure 2), the glucose units are 1-4 linked, meaning that the C-1 of
one glucose is linked by a glycosidic bond to the C-4 oxygen of the other glucose. The only
difference between them is in the configuration at the glycosidic bond. Maltose exists in
configuration, whereas cellobiose is .
Figure 1: Maltose

This disaccharide is 1,4--glucopyranosyl-glucopyranose. The 1-4 comes from the carbons

attached to the glycosidic bond. It is because carbon 1 and carbon 4 are trans to CH2OH. It is
glucopyranosyl because the first molecule is glucose. Glucopyranose comes from the second
molecule because it is glucose.
Figure 2: Cellobiose

This disaccharide is 1,4- - glucopyranosyl-glucopyranose. The 1-4 comes from the carbons
attached to the glycosidic bond. It is because carbon 1 and carbon 4 are cis to CH2OH. It is
glucopyranosyl because the first molecule is glucose. Glucopyranose comes from the second
structure because it is glucose.
Figure 3: Lactose

This disaccharide is 1,4- - galactopyranosyl-glucopyranose. The 1-4 comes from the carbons
attached to the glycosidic bond. It is because carbon 1 and carbon 4 are cis to CH2OH. It is
galactopyranosyl because the first sugar molecule is galactose. Glucopyranose comes from the
second structure because it is glucose.
How to Name Cyclic Polysaccharides
The most common polysaccharides are cellulose (Figure 1) and starch (Figure 2).
Figure 1: Cellulose

This polysaccharide is 1,4- -glucopyranose polymer. All of the individual sugars are glucose
so the prefix is gluco and they all contain 6 carbons so its a pyranose. It is because carbon 1
and carbon 4 are cis to CH2OH. The word polymer is added because its a chain of glucose.

Figure 2: Starch

This polysaccharide is 1,4- -glucopyranose polymer. All of the individual sugars are glucose so
the prefix is gluco and they all contain 6 carbons so its a pyranose. It is because carbon 1 and
carbon 4 are trans to CH2OH. The word polymer is added because its a chain of glucose.
Summary:

To determine acyclic carbohydrate name:

1. Determine the number of carbons.

2. Determine whether the molecule contains ketone or an aldheyde functional group.
3. Determine D or L configuration by looking at the position of the OH bonded to the last
stereocenter carbon.

To determine cyclic carbohydrate name:

1. Determine the number of carbons.

2. Determine whether the molecule contains ketone or an aldheyde functional group.
3. Determine or configuration by looking at the position of the OH that is attached to the
anomeric carbon and CH2OH.

Work Cited
Carbohydrates. <http://web.virginia.edu/Heidi/chapter7/chp7frameset.htm>.
Dr. Hardingers Thinkbook and Lecture Supplement
Metzker, Julia.Carbohydrates.
<http://chemphys.gcsu.edu/~metzker/Survey/Notes/16.Carbohydrates.html>.
Molecule Images from Google Images
Wikipedia